GB2198742A - Isoindoline compounds and pigment compositions - Google Patents
Isoindoline compounds and pigment compositions Download PDFInfo
- Publication number
- GB2198742A GB2198742A GB08728817A GB8728817A GB2198742A GB 2198742 A GB2198742 A GB 2198742A GB 08728817 A GB08728817 A GB 08728817A GB 8728817 A GB8728817 A GB 8728817A GB 2198742 A GB2198742 A GB 2198742A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- hydrogen
- compound
- chlorine
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 34
- 239000000049 pigment Substances 0.000 title claims description 27
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims description 12
- -1 methylmethoxy- Chemical class 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 229910052801 chlorine Chemical group 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000011368 organic material Substances 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 238000004040 coloring Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920005989 resin Chemical class 0.000 description 6
- 239000011347 resin Chemical class 0.000 description 6
- 239000004014 plasticizer Chemical class 0.000 description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XYQXGZLLGNQFSL-UHFFFAOYSA-N methyl 2,3,4,5-tetrachloro-6-cyanobenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N XYQXGZLLGNQFSL-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000485 pigmenting effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IGSKVMQALPYWSB-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-cyanobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N IGSKVMQALPYWSB-UHFFFAOYSA-N 0.000 description 1
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 1
- BDKUZCAWVKAITR-UHFFFAOYSA-N 2-(3-aminoisoindol-1-ylidene)-n-(4-chlorophenyl)-2-cyanoacetamide Chemical compound C12=CC=CC=C2C(N)=NC1=C(C#N)C(=O)NC1=CC=C(Cl)C=C1 BDKUZCAWVKAITR-UHFFFAOYSA-N 0.000 description 1
- MTKKGHVQPVOXIL-UHFFFAOYSA-N 3h-isoindol-1-amine Chemical compound C1=CC=C2C(N)=NCC2=C1 MTKKGHVQPVOXIL-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 241000282337 Nasua nasua Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 102100028522 Synaptophysin-like protein 2 Human genes 0.000 description 1
- 101710169339 Synaptophysin-like protein 2 Proteins 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
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- 229920001971 elastomer Polymers 0.000 description 1
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- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000001993 wax Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
1 - 11 V- 219 P 7,4 r) %.1 1 -T 'I Nove.1 c-ompositions ba_sed on
i.soind6Line pigments The inventIon re.lates to compositions Containing an isoindoline pigment and a sulfonated isoindoline compound, and to the use thereof for colouring high molecular we.ight org anic material.
Isoindoline pigments, which have long been used for colouring high molecular weight organic material (cf. for example DE-A-2,814,526, EP-A19,588. EP-A-62,614), do not always me.et the requirements of modern iddustry, in.particular in respect of their rheological properties.
It has now been fou nd that by adding certain sulfonated isoindoline compounds to isoindolin"e pigments the rheological behaviour of the latter is very-surprisingly improved.
The present invention accordingly provides a composition containing a) an isoindoline pigment of the formula I NC\ CONH-911.-.e :1 // 0 \ 11/ 0 >H i (I) in which R1 is hydrogen, halogen, methyl, Cl-C4-carbamoyl, Cl-C4alkanoylamino, unsubstituted or halogen-, methylmethoxy-, trifluoromethylor acetylamino-ringsubstituted benzoylamino.or phenylcarbamoyl or unsubstituted or chlorinesubjtituted phthalimide, R2 and R3 are independently of each other hydrogen, halogen, Cl-C4-alkyl or Cl-C4alkoxy, or R1 and R2. together with the phenyl radical to which they are bonded, form a benzimidazolone, quinazolone, dihydroxyquinazoline, phenmorpholone, quinolone or 4-methylquinolone radical, and Q is a group of the formula CN =< CONH-.,.' 13 9 in which R1', R21 and R31 are defined in the same way as Rj, R2 and R3 above, or is a group of the formula H I-N\ and b) a compound of the formula II Y 4 S03 e X I 0 \ 1 \ 11/ >H 6 R4 14 (11), in which R4 is hydrogen or chlorine, X9 is HG or'a group of the formula nO n or N E) (Rs (R6)(R7)(R8) m n(P is an n-valent metal cation, n is 1, 2 or 3, R5, R6, R7 and R8 are independently of one another hydroger,_ Cl-C18-alkyl, C5-C6-cycloalkyl, unsubstituted or Cl-C18-alkyl-substituted phenyl or R7 and R8, together wilh the N atom form a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R6, R7 and R8. together with the N atom, form a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, Y is hydrogen, halogen, methyl or amino and Z is one of the- groups of the formulae =< W // 0-0 111 1 CONH-J/ K \ 1%2 3 1.
o r // 0-0 \.=.x\soep Y in which Rj, R2, R, X(D and Y are.. as defined above or Z, if 31 R4 is chlorine, is oxygen.
- A halogen substituent is for e Xample fluorine, preferably bromine and in particul.ar chlorine.
A Cl-C4-carba.moyl R1 is for example aminocarbonyl, methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl or isopropylcarbamoyl. Preference is given to aminocarbonyl.
A Cl-C4-alkanoylamino R1 i-s for example formylami.no, acetylamino, propionylamino, n-butyrylamino or isobutyrylamino. Preference is given to acetylamino.
A Cl-C4-alky'I R2 or,R3 is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl or tert.-butyl. Preference is given to methyl.
A Cl-C4-aLkoxy R2 and R3 is for example methoxy, ethoxy, n-propoxy, nbutoxy or sec.-butoxy. Preference i given to methoxy.
A heterocycLic radical of the type defined as composed of R2, R3, R21 and R3' together with the phenyl radical to which they are bonded is for example benzimidazolon-5-yl, 6-chlorobenzi-midazolon-5-yl, 6methylbenzimidazolon-S-yl, quinazol-4-oh-6-yl, 2-methylquinazol-4-on-6-yl, quinazol-4-on7-yl, 2,4-dihydroxy-quinazolin-6-yl, phenmorphol-3-on-7-yl, phenmorphol-3-on-6-yl, 6-methylphenmorphol-3-on-7-yl, quinol2-on-6-yl, 4methylquinol-2on-7-yl, 7-chloro-4methylquinol2-on-6-yl or 4,8dimethylquin-ol-2 on-7-yl.
Q and Z are preferably a group of the formula =c / CN \ CONH-//_ 1 4h 13 %2 R, is preferably hydrogen. R2 is preferably bonded in the 4-position and preferably is hydrogen or chlorine. R3 is preferably bonded in the 3position and preferably is hydrogen or chlorine.
X 9 is preferably H(P or in particular a group of n(D the formula M n In a group X& of the formula M nG, MnS is for example n an alkali metal, alkaline earth metal, aluminium or transition metal cation, for example Nag. KG, Mg29. Ca 2G, Sr 2G Ba 2G, Mn 2(D, Cu2(b, N i2G, Cd2G, C03(1), A 139 and Cr 3G p but in particular an alkali metal or alkaline earth metal cation (n = 1 or 2) and preferably Ca 2(p.
A Cl-C18-alkyl substituent is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, tert.-butyl, n-pentyl, tert.-pentyl, hexyl, heptyL, octyl, decyl, dodecyl, tetradecyL, hexadecyl, heptadecyL or octadecyl.
R8 is f or o h e x y 1.
A Cl-C18-alkyl-substituted phenyl R5, R6, R7 and R8 is preferably C12-C18alkyL-substituted phenyl.
Specific examples of NG(R5MR6MR7MR8) are: NG)H4, NG)H3CH3, NGH2(CH3)2, NGH3C2H5, NGH2(C2H5)2, NGH3C3H7iso, N(9H3-cYcLohexyl, N H2-(cyclohexy02, NGH2(CH3)(C05), NGH3C6H5 N()H3-P-OctadecylphenyL and NG(CH3)4.
Of particular interest are compositions containing a) an isoindoline pigment of the formula A C5-C6-cYcloa example cyclopentyl or lkyl R5, R6, R7 and in particular cycl IQ NC /CONH- -R2 11 "R3 1 1 // 4 \ 11/ >H /R3 NU/ \CONH-,/ /-R2' in which R2, R3, R2' and R31 are inclepenclentLy of each other hydrogen or chLorine and b) a compound of the formuLa IV // 0 \ 0 \.=>\ S03 E) M SP >11 n /R3 Ncl CONH-O/ \-Rz lk.-. / (I I I), ( IV) in which R2 and R3 are as defined above, MnG) is an n-vaLent metaL cation and n is 1, 2 or 3.
Of very particuLar interest are compositions containing a) an isoincloLine pigment of the formuLa III as defined above and b) a compound of the formuLa IV in which R2 and R3 are as defined above and MnG is an aLkaLi metaL or aLkaLine earth 29 metaL cation (n = 1 or 2), but in particuLar Ca The isoincloLine pigments of the formuLa I are known and can be prepared by known methods.
The compounds of the formuLa II are noveL and comprise a further part of the subject-matter of the invention.
Compounds of the formuLa II in which Z is a group of the formuLa --c In 0 e. 1 "CONH-c is %2 3 are obtained analogously to processes known per se, for example by condensation of an iminoisoindoline of the formula NC\ CONH-c 0-0 e.
3 AH 9 in which Rj, R2 and R3 are as defined above, with an amine of the formula V H2 0 03H ( V) in which.Y is as defined above, in a molar ratio of 1:1, in acid solution, for example in glacial acetic acid, and if desired by subsequent reaction with a salt X(bLe in which XG is one of the groups MnG or NT(R5)(R6MR7)(R8) n as defined above and L8 is for example a hydroxyl, chloride, acetate or nitrate ion, likewise in a molar ratio of 1:1.
Compounds of the formula II in which Z is a group of the formula Y --- -N a // -) \.X\ 503 eH are obtained analogously to processes known per se, for examp by condensation of a diiminoisoindoline of the formula >B RH with an amine of the formula V in a molar ratio of 1:2 in 1 e acid soLution, for exampLe in gLaciaL acetic acid, and if desired by subsequ.ent reaction with a saLt X (9 Le.
Compounds of the formuLa I in which R4 is chLorine and Z is oxygen are obtained anaLogousLy to processes known per se, for exampLe by condensation of Lower aLkyL, preferabLy methyL, 3,4,5,6-tetrachLoro-2cyanobenzoate with an amine of the formuLa V in a moLar ratio of 1:1 in the absence of water in a poLar organic soLvent, preferabLy methanoL, ethanoL or isopropanoL, and in the presence of a base, for exampLe sodium methyLate or sodium ethyLate, and if desired by subsequent reaction with a saLt XSLG.
To prepare the compositions according to the invention, advantageousLy component a) is first conditioned in a conventionaL manner and suspended in water. Component b) is in generaL added in the form of a free suLfonic acid, and the saLt X G L 8 is added to obtain precipitation. It is aLso possibLe t.o mix component b) d'irectLy in.saLt form in aqueous suspension w.ith component a).
The mixing ratios of the components of-the compositions according to- the invention can vary within wide Limits. Preferred mixing ratios, however, range from 1 to 10% by weight of component b): 99 to 90% by weight of component a), but in particu Lar from 2 to 8% by weight -of component b): 98 to 92% by weight of component a) and preferabLy from 4 to 6% by weight of component b): 96 to 94% by weight of component a).
The addition of component b) can take pLace, before or after the conditioning of the pigment (component a). Conditioning is to be understood as meaning the preparation of a fine pariicLe form, for exampLe by aLkaLine precipitation, suLfuric acid precipitation, dry MiLLing with-or without saLt, soLvent or aqueous miLLing and preferabLy saLt kneading.
qepencling on the conditioning method or intended appLication, it can be of advantage to add to the pigment not onLy the amount of component b) required according to the invention but aLso certain amounts of textureimproving agents before or after the conditioning process. These comprise in particular fatty acids having at least 18 C atoms, for example stearic or behenic acid or their amides or metal salts, in particular Mg salts, and also plasticizers, waxes, resin acids, such as abietic acid, rosin soap, alkylphenols or aliphatic alcohols, such as stearyl alcohol or vicinal diols, such as dodecane-1,2-diol, and also modified rosin maleate resins or fumaric acid rosin resins. The texture-improving agents are preferably added in amounts of 0.1-30% by weight, in particular 2-15% by weight, based on the end product.
The compositions according to the invention are suitable for use as pigments for colouring high molecular weight organic material.
High molecular weight organic materials which can be coloured or pigmented with the compositions according to the invention are for example cellulose ethers and esters, such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as polymerization resins or condensation resins, such as amino resins, in particular urea- and melamineformaldehyde resins, alkyd resins, phenolic resins, poLycarbonates, polyolefins, polystyrene, polyvinyl chloride, poLyamides, polyurethanes, polyesters, rubber, casein, silicone and silicone resins, individually or mixed.
High moLecular weight organic materials in dissolved form for use as film formers also come into consideration, for example linseed oil varnish, nitrocellulose, alkyd resins, phenolic resins, melamine resins, acrylic resins and urea-formalde'hyde resins.
The high molecular weight organic compounds mentioned can be present individually or mixed as plastic compositions, melts or in the form of spinnable solutions, surface coatings, paints or printing inks. Depending on the intended use, it has proven advan.tageous to use the compositions according to the invention as toners or in the form of formulations. Based on the high molecular weight organic material to be pigmented, the compositions 9 - 4; according to the invention can be_used in an amount of 0.01 to 30% by weight, preferabLy 0.1 to 10% by weight.
The pigmenting of the high moLecuLar weight organic substances with the compositions according to the invention is effected for exampLe by mixing such a composition, if.desired in the form of a masterbatch, into these substrates using roLL miLLs or mixing or miLLing apparatus. The pigmented materiaL is then brought into the desired finaL form by methods known per se, such as caLendering., pressing, extruding, Coating, casting or injection mouLding. FrequentLy it is clesirabLe, if the mouLdings to be produced are not to be rigid or to reduce their brittLeness, to incorporate so-ca(Led pLasticizers in the high moLecuLar weight-compounds before mouLding. These pLasticizers can be for exampLe esters of phosphoric acid, phthaLic acid or sebacic acid. PLasticizers can be incor porated.into the poLymers before or after-incorporation' of the compo sitions according to the invention. It is aLso possibLe,. if different hues are to be obtained, to add to the high moLecuLar weight organic.'. materiaLs not onLy the compositions a'cco.rding to the invention but aLso fiLLers and other coLouring constituents, such as white, coLoured or bLack pigments, in any desired amount.
For pigmenting of paints and printing inks, the high moLecuLar weight organic materiaLs and the compositions according to the invention, if desired together with additives, such as fiLLers, other pigments, siccatives or pLasticizers, are fineLy dispersed or clissoLved in a common organic soLvent or soLvent mi xture. This can be done by dispersing or cli.ssoLving the individuaL components by themseLves or, aLternativeLy, severaL of them together, and onLy then combining aLL the components.
The coLorings obtained, for exampLe in pLastics, fibres, Paints or prints, are distinguished by good generaLproperties, such as good dispersibiLity, high transparency, good over-Lacquering, migration, heat, Light and weather re'si-stance, and the coLored pLastics exhibit absence of distortion.
In addition, the compositions according to the invention, compared with unmodified isoindoLine pigments, have improved tinctoriaL strength and in particular in paints and printing inks improved rheoLogy, Lower separation effects, such as floating in the presence of white pigments, a Lower flocculation tendency and, in surface coatings, a higher Lustre.
As a consequence of the good rheoLogicaL properties of the pigment mixtures according to the invention it is possible to produce paints having high pigment Loadings.
The compositions according to the invention are preferably suitable for coloring aqueous ano/or soLventcontaining paints, in particular automotive paints. Their use is very particularly preferred for metallic effect coati n g s.
The Examples which follow serve to illustrate the invention. Example 1: 3.23 g of 1-(cyano-p- chlorophenylcarbamoylmethylene)-3-iminoisoindoline and 1.73 g of metanilic acid are refluxed for 2 hours in 50 ml of glacial acetic acid. The resulting yellow reaction product is fi-l.tered off at 800C and washed with methanol and water to give, after drying, 3.1 9 of the dye of the formula -. t, t.-cl NC\ k = & S03 e NH4 Analysis for C23H18N504CIS c calculated: 55.7% found: 56.0% H N S c 1 3.63% 14.12% 6.46% 7.16% 3.69% 13.82% 5.68% 7.57% - 11 1 4 Example 2: 6.0 g of methyL 3,4,5,6-tetrachLoro-2-cyanobenzoate are added to a solution of 40 mL of methanol and 1.08 g of sod'ium methyLate. The mixture is stirred for half an hour. A solution of 3.46 g of metaniLic acid, 1.08 g of sodium methyLate and 30 mL of methanol is then added and stirred in at room temperature for 15 hours. This is foLLowed, while stirring, by refLuxing for 3 hours, acidifying with 2.5 mL of acet-ic acid and a further 2 hours under reflux. The reaction product is filtered off at room temperature, washed with a Lit tLe methanol and dried to give 7.0 g of a yellow dye of the formula C ,\., C\ d \". /.
L 8 \ S03 E) Na E ').
Analysis for C14H5C10204SNa c H N S 1 calculated: 36.36% found:
08% 6.06% 6.93% 35.55% 1.61% 5.83% 6.98% Example 3: 6.0 g of methyl 3,4,5,6-tetrachloro-2- cyanobenzoate are reacted with 1.08 9 of sodium methylate in 40 ml of methanol as described in Example 2. To the solution obtained are added 1. 9 9 of 1,4-phenylenediamine-2sulfonic acid, 0.54 g of sodium methylate and 30 ml of methanol. The result is an orange-brown solution which is stirred at room temperature for 3 hours. This is followed, 12 while stirring, by refluxing for 3 hours, acidifying with 2.5 ml of acetic acid and a further 2 hours under reflux. The precipitated reaction product is filtered_off hot, washed with a little methanol and dried to give 4.1 g of a yellow dye of the formula 0-0 \% Y1 - \-NH? C 1 /A a /0 1 11 H d 0 M 0 "\ - > 1 8 17.3 g a c e t i c \ S03eNaO Analysis for C14H6C10304SNa c H N S c 1 calculated: 35.25% 1.27% 8.81% 6.72% 29.72% found: 35.07% 1.99% 8.33% 6.2 % 28.5 % Example 4: 9.1 9 of 1,3-diiminoisoindoline (80% pure) and of metanilic acid are stirred in 175 mI of glacial room temperature for 3 hours and at the reflux a further hour. The resulting yellow dye is washed with glacial acetic acid and acetone 21.2 9 of the ammonium salt of the dye of acid at temperature for filtered off hot, and dried to give the formul \S03H if />H SC3H Analysis for C20H15N306S2 x NH3 X H20 H N S 4.06% 11.38% 13.0% 4.43% 10.87% 13.19% calculated: f o u n d: Example 5:
48.78% 49.1% a) A mixture of 12.8 9 of phthalonitrile, 19.45 g of cyanoacet-4-chloroanilide, 27.5 g of cyanoacet-3,4-dichloroan- 13 ilide, 13.82 g of ground potassium carbonate and 0.8 g of tricaprylmethylammonium chloride in 300 ml of methanol is.heated to 1000C in the course of 6 hours. The suspension is stirred at 1.00oC forl hour, then cooled down to 700C and slowly added in the course of 10 minutes to a warm mixture of 8.4 ml of acetic acid and 200 mI of methanol at 400C. After 15 hours of boiling.under reflux, the pigment obtained is filtered off, washed with 600 ml of warm methanol and with 250 mI of warm water- and dried to give 52.1 9 of an orange mixture chiefly comprising the pigment of the formula cl NC\ CONH-eo \\.-Cl 0 / \ = / 11 @// 0 \ 0 /. >H 1 J1 11 0 /Y 0-0 Ne \C6NTH-o/ \.-cl b) 16.2 9 of the moist press cake obtained as per a) (30.9% dry content) are thoroughly dispersed in 100 mI of water and heated to 700C. 0.25 g of the compound of Example 1 is then added. After half an hour of-stirring at 700C, 1.32 g of CaCL2 x ?-H20 are added, and after a further half hour stirring the product is filtered off at 700C and dried to give 5.15 g of an orange pigment mixture.
Incorporating the mixed pigment thus obtained in an alkyd paint system ( U,1Setal 84, Kunstharzfabriek Synthesis R.V., Holland; solids content: 70% by weight) gives strong orange surface coatings of high lustre and good allround resist-ances. Example 6: Example 5b is repeated, except that the compound of Example 1 is replaced by the compound of Example 2, affording an orange mixed pigment having equally good properties as that of Example 5b. Example 7: Example 5b is repeated, except that the compound - 1L - of Example 1 is replaced by the compound of Example 3, affording an orange mixed pigment having equally good properties as that of Example 5b. Example 8: Example 5b is repeated, except that the compound of Example 1 is replaced by the compound of Example 4, affording an orange mixed pigment having equally good properties as that of Example 5b.
- is
Claims (11)
1. A composition containing a) an isoindoline pig,m.ent of the formula 1 NC CONH-JO\R2 JO\ /0 3 1 if H v.
( 1) in which R, is hydrogen.. halogen, methyl.. Cl-C4-carbamoyl.._ Cl-C4-a lkanoylamino. unsubstituted or halogen-, methylmethoxy-, trifluoromethyl- or acetylam'lno-ringsubstituted benzoylamino or phenylcarbamoyl or unsubstituted or chlorinesubstituted phthalimide, R2 and R3 are independently of each other hydrogen, halogen, Cl-C4-alkyl or Cl-C4- alkoxy, or R1 and R2. together with the phenyl. radical to which they are bonded, f.orm a benzimidazolone, quinazolone, dihydroxyquinazoline, phenmorpholone, quinolone or 4-methylquinolone rad ical, and Q is a group of the formula - CN =C/ / \CONH- 131 1 3 in which R1', R2' and R31 are defined in the same way as Rj, R2 and R3-above, or is a group of the formula 9 H =S/ --N \0==0 1 \0 - _x ', ' 8 11 and j b) a compound of the 16 - formula II R4 4 - G//_ 0 4 S03 y in which R4 is hydrogen or chlorine, X(') is H(E) or a group of the formula m nE) n or N E) (Rs)(R6)(R7)(R8).
MrG is an n-valent metal cation, n is 1,
2 or 3, R5, R6, R7 and R8 are independently of one another hydrogen, Cl-C18-alkyl, CS-C6-cycloalkyl, unsubstituted or Cl-C18-alkyl-substituted phenyl or R7 and R8, together with the N atom form a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R6, R7 and R8, together with-the N atom, form a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, Y is hydrogen, halogen, methyl or amino and Z is one of the groups of the formulae CN =< CON!! 13 o r 1 =N-oll"-0.
\0 =.X\ S03 (D X (D in which Rj, R2, R3, Xe and Y are as defined above or Z, if R4 is chlorine, is oxygen.
t 2.
A composition accordi.ng to claim 1, which contains a) an isoindoline pigment of the formula III i // 0-0 \\ NC CONH7 /.-RZ 11 0 / 0 \ / 0 >H \R3 1 11 k. / \ 11 - /R3 2 a NC/ \ COM-/ /O-R2, in which R2, R3, R21 and R31 are independently of each other hydrogen or chlorine and b) a compound of the formula IV M t 0 0-0 no S03 n 1 11 H
3 Ne \CONH-c/ (IV) in which R2 and R3 are as defined above, M nS is an n-vaLent metal cation and n is 1, 2 or 3.
A composition according to cLa'im 2, which contains a) an isoindoLine pigment of the formula III as defined in cLaim-2 and b) a compound of t"he formula IV as defined in claim 2 in which R 2 and R3 are as defined in claim 2.. MnG is an alkali metal or alkaline earth metal cation and n is 1 or 2.
4. A composition according to c1aim 2, which cont-a ins - a) an isoindoLine pigment of the formula III as defined in claim 2 and b) a compound of the formula IV as defined in claim 2 in which R2 and R3 are as defined in cLaim 2 and M nO is a caLcium cation.
5. A composition according to cLaim 1,-wherein the mixing ratio of component a): component b) is 99 to 90% by weight: 1 to 10% by weight.
6. A process for coloring high molecular weight organic material, which comprises using a composition according to claim 1.
7. A high molecular weight organic material containing a composition according to claim 1.
8. A compound of the formula II Y 4 C J_ 0 S03 E) X 0 R4 V v R4 14 (11) in which R4 is hydrogen or chlorine., Xe is H(P or a group of the formulae nE) n o r N E) (P%S)(R6)(R7)(R8) m n)is an n-valent metal cation, n is 1, 2 or 3, R5, R6, R7 and R8 are independently of one another hydrogen, Cl-C18-alkyl, CS-C6-cycloalkyl, unsubstituted or C.1-C18alkyl-substituted phenyl or R7 and R8, together with the'N atom form a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R6, R7 and R8, together with the N atom, form a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, Y is hydrogen, halogen, methyl or amino and Z is one of the groups of the formulae CN Y =< or CON!! SO 3V, 3 in which Rj, R2, R3., X(') and Y are as defined above or Z, if R4 is chlorine, is oxygen.
19 -
9. A compound according to claim 8, of the formula IV v S03 e n /R3 NC/ \CONH-/ = \ --R2 k -.// ( I V) in which R2 and R3 are-independently of each other hydrogen or chlorine, Mn@ is an n-valent metal cation and n is 1, 2 or 3.
10. A compound according to claim 9, wherein Mn9 is an alkali metal or alkaline earth metal cation and n is 1 or 2.
11. A compound according to claim 9, wherein M n(g is a calcium cation FO 7.31BUElaeg 1 Published 1988 at The Patent Office, State House, 66171 High Holborn, London WClR 4Tr..-rurther copies may be obtained from The Patent Office, Sales Branch. St Me -_v Cray, Orpington. Nent BRS 3R.D. Printed by MultiPlex techniques ltd. St Mary Cray. Kent. Con. 1 187.
i--b oz, vp m, nrnimnon- Nent BR5 3RD. Printed bv MultiWex teelinioues ltd. St Mary urkv neflL. UOn- I'Ll' -
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH505586 | 1986-12-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8728817D0 GB8728817D0 (en) | 1988-01-27 |
| GB2198742A true GB2198742A (en) | 1988-06-22 |
| GB2198742B GB2198742B (en) | 1990-07-18 |
Family
ID=4287207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8728817A Expired - Lifetime GB2198742B (en) | 1986-12-17 | 1987-12-09 | Novel compositions based on isoindoline pigments |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4764217A (en) |
| JP (1) | JPS63161061A (en) |
| DE (1) | DE3742388A1 (en) |
| FR (1) | FR2610941B1 (en) |
| GB (1) | GB2198742B (en) |
| IT (1) | IT1223490B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0272216B1 (en) * | 1986-12-17 | 1992-08-19 | Ciba-Geigy Ag | Compositions of matter based on tetrachloroisoindolinone pigments |
| US4892899A (en) * | 1987-12-08 | 1990-01-09 | Ciba-Geigy Corporation | Novel compositions based on tetrachloroisoindolinone pigments |
| DE3914384A1 (en) * | 1989-04-29 | 1990-10-31 | Basf Ag | PIGMENT PREPARATIONS AND THEIR USE |
| US5177209A (en) * | 1991-04-22 | 1993-01-05 | Miles Inc. | Process for preparation of asymmetric isoindoline pigments |
| CH685162A5 (en) * | 1991-05-07 | 1995-04-13 | Ciba Geigy Ag | Pigment compositions. |
| DE4115841B4 (en) * | 1991-05-15 | 2004-11-04 | Schölly Fiberoptic GmbH | Device for the optical inspection of objects |
| CN101896556A (en) * | 2007-12-10 | 2010-11-24 | 巴斯夫欧洲公司 | Isometric isoindoline yellow pigment |
| KR102436376B1 (en) * | 2016-07-07 | 2022-08-25 | 스미또모 가가꾸 가부시키가이샤 | Pigment composition, colored composition and colored curable composition |
| JP6996282B2 (en) * | 2017-12-22 | 2022-01-17 | 東洋インキＳｃホールディングス株式会社 | Coloring compositions for color filters, color filters and pigment dispersants |
| EP3798271A1 (en) | 2019-09-30 | 2021-03-31 | BASF Colors & Effects GmbH | Isoindoline derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532687A (en) * | 1968-03-22 | 1970-10-06 | Geigy Ag J R | Tetrahalogeno isoindoline pigments |
| CH625542A5 (en) * | 1977-04-07 | 1981-09-30 | Ciba Geigy Ag | |
| US4384057A (en) * | 1979-05-14 | 1983-05-17 | Ciba-Geigy Corporation | Composition containing a condensation product of 1,3-diiminoisoindoline and cyanoacetic anilide used to pigment an organic lacquer resin |
| US4426533A (en) * | 1981-04-06 | 1984-01-17 | Ciba-Geigy Corporation | Process for producing bismethine isoindolines |
| DE3327563A1 (en) * | 1983-07-30 | 1985-02-07 | Basf Ag, 6700 Ludwigshafen | COLORFUL ISOINDOL PIGMENTS, THEIR PRODUCTION AND USE |
| EP0132818B1 (en) * | 1983-07-30 | 1986-12-30 | BASF Aktiengesellschaft | Isoindoline pigments having a strong colouring capacity, their preparation and their use |
| CH668978A5 (en) * | 1985-06-26 | 1989-02-15 | Basf Ag | ISOINDOLINE DYES. |
-
1987
- 1987-12-07 US US07/129,577 patent/US4764217A/en not_active Expired - Fee Related
- 1987-12-09 GB GB8728817A patent/GB2198742B/en not_active Expired - Lifetime
- 1987-12-14 DE DE19873742388 patent/DE3742388A1/en not_active Withdrawn
- 1987-12-15 FR FR878717456A patent/FR2610941B1/en not_active Expired - Lifetime
- 1987-12-16 IT IT23044/87A patent/IT1223490B/en active
- 1987-12-17 JP JP62317670A patent/JPS63161061A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63161061A (en) | 1988-07-04 |
| DE3742388A1 (en) | 1988-06-23 |
| FR2610941B1 (en) | 1990-08-24 |
| GB8728817D0 (en) | 1988-01-27 |
| US4764217A (en) | 1988-08-16 |
| FR2610941A1 (en) | 1988-08-19 |
| GB2198742B (en) | 1990-07-18 |
| IT8723044A0 (en) | 1987-12-16 |
| IT1223490B (en) | 1990-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19951209 |